This invention relates to o-haloalkylbenzene sulfonyl ureas which are useful as herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.1 is H,F,Cl or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.2 is H or CH.sub.3 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ; PA1 R.sub.4 is H or C.sub.1 -C.sub.4 alkyl; PA1 R.sub.3 and R.sub.4 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sub.4 ' is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl optionally substituted with 1-3 atoms of F, Cl or Br, or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.6 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.7 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.8 is H, CH.sub.3 or OCH.sub.3 ; PA1 A is ##STR6## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; PA1 Y is CH.sub.3 or OCH.sub.3 ; PA1 Z is N, CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA1 Y.sup.1 is H, CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and PA1 Q is O or CH.sub.2 ; PA1 and their agriculturally suitable salts; PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ; PA1 (3) when W is S, then R.sub.8 is H; and PA1 (4) when L is F, then R.sub.1 is H, F, or C.sub.1 -C.sub.4 alkyl. PA1 (1) compounds of generic scope wherein Z is N, CH, CCl, CBr or CCH.sub.3, W is O, and R.sub.8 is H or CH.sub.3 ; PA1 (2) compounds of preferred (1) wherein Z is CH or N and X is CH.sub.3 of OCH.sub.3 ; PA1 (3) compounds of preferred (2) wherein A is ##STR7## L is Cl, Br or NR.sub.3 R.sub.4 and R.sub.8 is H; (4) compounds of preferred (3) wherein R.sub.1 and R.sub.2 are H; PA1 (5) compounds of preferred (4) wherein R is H; and PA1 (6) compounds of preferred (5) wherein L is Cl or Br. PA1 2-(Dichloromethyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benze nesulfonamide; PA1 2-(Dichloromethyl)-N-[(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]benzenesul fonamide; PA1 2-(Dichloromethyl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl] benzenesulfonamide; PA1 2-(Chloromethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzene sulfonamide; PA1 2-(Chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulf onamide; PA1 2-(Chloromethyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfon amide; PA1 2-(1-Chloroethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzen esulfonamide; PA1 2-(1-Pyrrolidinylmethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benz enesulfonamide, hydrochloride; and PA1 2-(1-Pyrrolidinylmethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benz enesulfonamide. PA1 Z is CH or N; PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when L is NR.sub.3 R.sub.4 or N.sup.+ R.sub.3 R.sub.4 R.sub.4 ', then R.sub.3 or R.sub.4 can not be H; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3. PA1 (1) when R.sub.1 is Cl, then L is Cl or Br and R.sub.2 is H; PA1 (2) when L is NR.sub.3 R.sub.4 or N.sup.+ R.sub.3 R.sub.4 R.sub.4 ', then R.sub.3 and R.sub.4 cannot be H; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3. PA1 L is as defined for Formula II; PA1 Z is CH or N; and PA1 R.sub.9 is C.sub.1 -C.sub.3 alkyl. PA1 (a) The compound of Formula II can be suspended or dissolved in an alkanol solvent, R.sub.9 OH, in the presence of at least two equivalents of alkoxide, --OR.sub.9. The alkoxide can be added directly as alkali metal or alkaline earth metal alkoxide or can be generated by the addition to the alkanol solvent of at least two equivalents of a base capable of generating alkoxide from the solvent. Suitable bases include, but are not limited to, the alkali and alkaline earth metals, their hydrides and tert-butoxides. For example, when R.sub.9 is methyl, the compound of Formula II could be suspended or dissolved in methanol in the presence of two equivalents of sodium methoxide. PA1 (b) Alternatively, two equivalents of sodium hydride could be used in place of the sodium methoxide. The compound of Formula II can be suspended or dissolved in an inert solvent in the presence of at least two equivalents of alkoxide, --OR.sub.9. Suitable inert solvents include, but are not limited to, acetonitrile, THF and dimethylformamide. The alkoxide may be added directly as alkali metal or alkaline earth metal alkoxide or may be generated from alkanol and a base as described in (a) above. For example, when R.sub.9 is methyl, the compound of Formula II could be suspended or dissolved in THF in the presence of two equivalents of sodium methoxide. Alternatively, two equivalents each of methanol and sodium hydride could be used instead of sodium methoxide.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug Res. 6, 123 (1974). ##STR2## wherein R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists, however, for more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.
In U.S. Pat. No. 4,127,405 compounds of the following formula are taught: ##STR3## wherein R.sub.1 is ##STR4## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA2 R.sub.5 is hydrogen, fluorine, chlorine, bromine methyl or methoxy; PA2 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms; PA2 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA2 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA2 W and Q are independently oxygen or sulfur; PA2 n is 0, 1 or 2; PA2 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA2 Z is methyl or methoxy; PA2 or their agriculturally suitable salts; PA2 provided that:
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA3 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA3 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen.